Sodium borohydride → HCID 13849495, compound

HRID 978117Notes

Reaction equation

HRID 978117 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18](=[O:20])[CH3:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH:18]([OH:20])[CH3:19])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13849489HCID 13849489, compound

Product 1

HCID 13849495HCID 13849495, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a mixture of ethyl-3-methyl-4-(2-oxopropoxy)benzofuran-2-carboxylate (1.9 g, 6.8 mmoles, Example 117) in ethanol (100 ml) at 5° C. was added in portions, sodium borohydride (254 mg, 6.8 mmoles). The mixture was stirred for 10 minutes at 5° C. and 30 minutes at room temperature. The reaction was quenched with saturated ammonium chloride solution (1.5 ml) and concentrated. The residue was taken up in ether (100 ml), washed with water (25 ml), dried with Na2SO4, filtered and concentrated to obtain the title compound as an oil which crystallized on standing. The crystals were stirred with 25% ether in hexane (50 ml) for 30 minutes, filtered and then air dried, m.p. 94°-96° C.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution (1.5 ml)
  2. concentrationconcentrated
  3. washwashed with water (25 ml)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8ec02821d77d4bbd9a84638053fa146d
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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